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[This series intends to introduce you to each of the legitimate Chicago Cubs GM candidates, and give you a quick, clean rund0wn of the most important information to know about that candidate as the Cubs’ search process continues. Previously: Brian Cashman.]

Name and Age: Theo Epstein, 37.

Current Role and Contract Status: Boston Red Sox General Manager since November 2002, signed through 2012. He currently makes something north of $1.5 million per year.

Record in Current Role: The Red Sox have made the playoffs every year under Epstein except for last year and 2006. They won the World Series twice (2004 and 2007). Even in the two non-playoff years, the Red Sox were 10 and 16 games over .500.

Notable Prior Experience: Epstein cut his teeth in the San Diego Padres’ organization, first doing public relations, and then taking over baseball operations. He picked up his law degree at the University of San Diego while he was working for the Padres.

Reason(s) for Including as Candidate: Big market GM, very successful, and, having ended the Red Sox’s “curse,” is inextricably tied to the fate of the Chicago Cubs in the minds of many. Also, Tom Ricketts wants to emulate the “Boston Red Sox model,” which is another way of saying, “I want to do it like Theo Epstein has done it.”

Pros/Hype: This is the guy who FINALLY won it all for the Boston Red Sox. And, make no mistake, that 2004 squad was his team, which he started building when he took the reigns after the 2002 season. Since then, the Sawx have done nothing but win and make money hand-over-fist. He has changed the culture in Boston, and, after doing so, has ably dealt with the dangerously high expectations his own success engendered. At the close of the last decade, Epstein was honored with a slew of “best executive of the decade” type awards.

Cons/Cynical Criticism: Like his counterpart in New York, Epstein has been giving a huge freaking checkbook with which to work. It’s easy to cover mistakes when you’ve got all that green backing you up – mistakes like John Lackey, Daisuke Matsuzaka, Carl Crawford, etc. Also, Epstein is under contract for 2012, and Boston ownership has not given any indication that they will allow him to step out for interviews. The Cubs would have to, at a minimum, wait out the Red Sox season before being able to talk to him, at which time he could easily tell them, “not interested.”

Desirability: Very high. Just like with Cashman, I get the cynicism. But – once again like Cashman – Epstein faces unbelievable pressure from the owners, the media, and the fans in Boston. And, unlike Cashman, that pressure is almost exclusively the product of Epstein’s own efforts. So successful has he been that his progeny are littered through MLB front offices, and most are themselves considered desirable GM targets. The Red Sox roster is made up not only of expensive free agents, but also brilliantly-developed Boston talent, as well as players acquired by way of other Boston talent.

Likelihood/Probable Outcome: With the Red Sox’s current swoon, the chances that Epstein would consider taking an interview with the Cubs (if he was even permitted to do so) have crept up slightly from “highly unlikely” to “maybe.” I still don’t think he would ultimately take a job with the Cubs, even if he were offered a president-level position (which Tom Ricketts has suggested isn’t going to happen for any candidate). I do, however, believe Epstein is one of a handful of candidates at the top of Ricketts’ list, for whom Tom is ready and willing to wait the season out. Ricketts will get in Epstein’s ear if he really wants to – but it remains dubious that the outcome would be anything more than a better title and more money from the Red Sox for Epstein.

nice piece ..it gets me wondering what an Epstein led Chicago front office would look like and how successful he could be here *if* he can do it his way

Fishin Phil

As much as I would love to see Epstein come here, I agree that it is still highly doubtful.

Toosh

Hughes just resigned. Rather than being fired?

Fishin Phil

Dang Toosh, you are fast! Nice find.

Toosh

Thank you! I (Sorry, Brett) read other websites.

http://www.bleachernation.com Brett

I love when Toosh scoops me. Gives me more time to put a thoughtful post together, rather than scrambling to be “first.”

Toosh

As I’m sure you know, Brett, it’s never my intent to scoop you. Nor am I interested in being the first to post information. I apologize if my posts don’t appear to be thoughtful. If I come across some news that I think Bleacher Nation readers might be interested in, I come to your website and share it. If it hasn’t been posted already.

Jeff

Don’t apologize because Brett’s slow on the trigger. We want our news now, and we want to discuss it now. He’ just lollygagging with the story until he can come up with a clever anecdote about all those awesome shirts that we always saw Gary Hughes wearing.

http://www.bleachernation.com Brett

Never apologize for that, Toosh. I mean what I said: I love that you post stuff as you find it. It’s a big help, and I know other people really appreciate it.

TWC

Ray-Bob, I can only imagine that he meant that he appreciates your willingness to post news items as quickly as you do, not that your efforts betray any lack of thoughtfulness.

Plus, as many of you know, Ace’s real money comes from selling refurbished/retro My Little Ponies on his eBay store, and that’s where his attentions necessarily lie.

http://www.bleachernation.com Brett

Oh, yeah, Toosh: when I said it relieves me of having to be “first,” I didn’t mean you were all about being “first” – I was talking about other sites. You’re all good.

Toosh

Ray-Bob! I like it! The missing “Walton”? Yikes. No problem here. On another note, I was going to come down to the game tomorrow with a Brewer friend of mine so he could see them clinch the division, but that plan changed. We are going to Milwaukee’s Saturday night game.

TWC

Haven’t I been calling you Ray-Bob since you switched to Toosh? Or has that just been all in my head? Now I’m worried…

http://www.bleachernation.com Brett

You have, it’s just that Toosh – like the rest of us – is incredibly good at ignoring you.

Toosh

Oldtimer’s Disease! What were we posting about?

http://www.michigangoat.blogspot.com MichiganGoat

In keeping with our slang… ya just got pwned TWC

TWC

I like your site because the witticisms are short and barbed.

http://www.michigangoat.blogspot.com MichiganGoat

I like Toosh’s posts because they are short and informative

http://www.michigangoat.blogspot.com MichiganGoat

Not mention first

http://Bleachernation Dan Ballard

My only concern with Epstein or Cashman is mentioned in the article. They both have always been one and two in payroll. Could either one of them do it with our payroll?

Toosh

With one of the highest revenue streams and payrolls in the NL, the Cubs should have one of the best farm systems and Major League rosters in the NL as well.

http://www.bleachernation.com Brett

I am less concerned about it given how much the Cubs outspend their NL Central counterparts in recent years. That should give the incoming guy plenty to work with, relative to his nearest playoff competitors.

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